Acetic Anhydride → HCID 53660973, compound

HRID 1578814Notes

Reaction equation

HRID 1578814 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:27])[CH2:10][CH2:11][CH:12]([OH:26])[CH:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:3][CH2:4][OH:5].[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:28]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:27])[CH2:10][CH2:11][CH:12]([OH:26])[CH:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54036469HCID 54036469, compound

Product 1

HCID 53660973HCID 53660973, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3,7,11,15,19-pentamethyl-2,6,14,18-eicosatetraene-1,10-diol (3.75 g) in pyridine (1 ml) while cooling with ice, acetic anhydride (1.53 g) is dropwise added in 15 minutes, and then stirring is continued for 40 minutes. The reaction mixture is poured into ice water and extracted with ether. The ether extract is washed with water, dried and evaporated. The residue (3.9 g) is purified by chromatography on silica gel (40 g) using benzene to give 1-acetoxy-3,7,11,15,19-pentamethyl-2,6,14,18-eicosatetraen-10-ol (3.1 g).

Workup

  1. additionis dropwise added in 15 minutes
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. customdried
  6. customevaporated
  7. customThe residue (3.9 g) is purified by chromatography on silica gel (40 g)

Sources & evidence

ORD record
ord-3c5e642644294f0992b6bcf7c6578aa5
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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