Acetyl chloride → HCID 54039037, compound

HRID 2396140Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][N:44]([CH3:46])[CH3:45])=[CH:37][CH:36]=2)(O)[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:22][CH:21]=2)[CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C>C(OC(=O)C)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:35]2[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][N:44]([CH3:46])[CH3:45])=[CH:39][CH:40]=2)=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:22][CH:21]=2)[CH2:17][CH2:18][OH:19])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture containing 5.8 g of 1,2-bis(4-benzyloxyphenyl)-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butan-1,4-diol and 20 ml of acetic anhydride is heated at 90° C. for 1 hour. 3.7 g of acetyl chloride is added and the mixture is heated at 80° C. for 0.5 h. The solvent is evaporated. 0.75 g of sodium hydroxide in 200 ml of 80% methanol is added and the mixture is refluxed for 3 hours. The mixture is allowed to cool to room temperature. The crystallized product is collected by filtration. The yield is 4.7 g (83%).

Workup

temperaturethe mixture is heated at 80° C. for 0.5 h
customThe solvent is evaporated
addition0.75 g of sodium hydroxide in 200 ml of 80% methanol is added
temperaturethe mixture is refluxed for 3 hours
temperatureto cool to room temperature
filtrationThe crystallized product is collected by filtration

Sources & evidence

ORD record: ord-7e7c266592d24332b5aa8135a2033063
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491173

Reaction notes

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