Bromopropanol → 3-{3-[3-(3-Hydroxypropyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic Acid

HRID 584260Notes

Reaction equation

HRID 584260 reaction equation
[OH:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][C:26]([O:28]CC)=[O:27])[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Br[CH:32]([OH:35])[CH2:33][CH3:34]>>[OH:35][CH2:32][CH2:33][CH2:34][O:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 12887879BromopropanolHCID 69792380Ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl)acrylate

Product 1

HCID 697928943-{3-[3-(3-Hydroxypropyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic AcidYield 49.7%

Procedure

In a manner similar to that of Example 16(a), by reaction of 1.2 g (2.9 mmol) of ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl]acrylate obtained in Example 13(f) with 490 mg (3.5 mmol) of 1-bromopropanol, 632 mg (47%) of the expected compound were obtained in the form of a yellow oil.

Sources & evidence

ORD record
ord-be73c93414134113b62f06bd2e33a191
Source dataset
uspto-grants-2005_08
Patent number
US06924388B2

Reaction notes

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