Hydrochloric Acid → Ethyl 2-chloro-3-[4-(6-ethoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]propionate

HRID 1030433Notes

Reaction equation

HRID 1030433 reaction equation
N[C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]2([CH3:24])[CH2:17][CH2:16][C:15]3[C:10](=[C:11]([CH3:23])[C:12]([CH3:22])=[C:13]([O:19][CH2:20][CH3:21])[C:14]=3[CH3:18])[O:9]2)=[CH:4][CH:3]=1.[ClH:27].N([O-])=O.[Na+].[C:32]([O:36][CH2:37][CH3:38])(=[O:35])[CH:33]=[CH2:34]>CC(C)=O>[Cl:27][CH:33]([CH2:34][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]2([CH3:24])[CH2:17][CH2:16][C:15]3[C:10](=[C:11]([CH3:23])[C:12]([CH3:22])=[C:13]([O:19][CH2:20][CH3:21])[C:14]=3[CH3:18])[O:9]2)=[CH:4][CH:3]=1)[C:32]([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 198221972-(4-Aminophenoxymethyl)-6-ethoxy-2,5,7,8-tetramethylchromanHCID 23668193Sodium Nitrite

Product 1

HCID 19822269Ethyl 2-chloro-3-[4-(6-ethoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The procedure described in Preparation 64 was repeated, except that 9.5 g of 2-(4-aminophenoxymethyl)-6-ethoxy-2,5,7,8-tetramethylchroman (prepared as described in Preparation 63), 10 ml of concentrated hydrochloric acid, 2.4 g of sodium nitrite, 26.8 g of ethyl acrylate, 0.4 g of cuprous oxide and 100 ml of acetone were used as the starting materials, to give the title compound.

Workup

  1. customThe procedure described in Preparation 64

Sources & evidence

ORD record
ord-aca3391237b24c81b5b1d395ff756efc
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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